CADET ______SECTIONIHR TIME OF DEPARTURE _ DEPARTMENT OF CHEMISTRY & LIFE SCIENCE CH383, AY 08-1 McMurry, Organic Chemistry, t h ed. WPR III, AlC Hour Chapters 7-9, Experiment 5 20 November 2007 120 minutes INSTRUCTIONS 1. Do not mark on this exam or open it until "begin work" is given. 2. Solve problems in the space provided. SHOW ALL WORK. ANSWER ALL QUESTIONS. 3. Molecular model kits are permitted; however, models may only be assembled after "begin work" is given. The molecular model instruction booklet is not permitted. Calculators are not authorized. RDCs are authorized. 4. There are 13 pages in this exam. Report any illegible or missing pages to the OIC in the hallway. Write your name in the spaces provided. (TOTAL WEIGHT: 200 POINTS) DO NOT WRITE IN THIS SPACE PROBLEM MAX SCORE CUT YOUR SCORE I 40 II 60 III IV 30 V EXTRA CREDIT 20 TOTAL GRADE 200

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---------Name:Problem II, Reactions, 60 Points (20) 1. Complete four of the following five boxes for the following tree of reactions by giving the major products and put an "X" in the box you do NOT want graded: H2~+P~:1CH3 36=:CH2 1.BH3 2. oIr,H2~,H20CH383, AY 08-1 4 WPRIII, AlC Hour

--------------Name: Problem II, continued (20) 2. Complete four ofthe following five reactions with the correct reactant. Indicate stereochemistry as appropriate. Cross out the reaction you do not want graded by placing a large "X" through the entire reaction. a. b.

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